The email came on Day 73, while I was sitting in the airport preparing for Rejection #134.
Subject: Re: Your Ridiculous Request
David,
I've been thinking about your proposal to write a monthly column for our magazine. My initial response was no – you have no journalism experience, no published clips, and frankly, your pitch was amateur at best.
But I can't stop thinking about it. Your rejection experiment is exactly the kind of counterintuitive story our readers need. The authenticity in your writing sample was refreshing.
Let's try one article. 1,500 words on what your first 100 rejections taught you. If readers respond well, we'll discuss a regular column.
Are you insane enough to say yes to this?
- Patricia, Editor-in-Chief
I read it three times. This was supposed to be Rejection #96. I'd pitched five major magazines with the same proposal, collecting form rejections from four. Patricia's magazine was the biggest reach, the one I was certain would either ignore me or send the harshest rejection.
Instead, she was offering me a writing gig at a national publication.
"You look confused," said the woman sitting next to me at the gate.
"I'm supposed to be collecting rejections," I explained. "But people keep saying yes to ridiculous things."
She laughed. "Maybe you're bad at being bad at things."
That gave me an idea. I turned to her. "This is going to sound crazy, but would you be willing to switch seats with me on the plane? I want your first-class seat."
"You want me to give up my first-class seat for your economy ticket?"
"Yes. I know it's absurd. I'm conducting an experiment in—"
"Deal."
I stared at her. "What?"
"I said deal. I hate flying first class. Too much attention from flight attendants. I just want to read my book in peace. You're doing me a favor."
Rejection #134: Failed. Unexpected Upgrade #8: Success.
This was becoming a problem. The better I got at asking, the more people said yes. My rejection-to-acceptance ratio was tilting in the wrong direction.
The first-class flight gave me time to analyze the pattern. I pulled out my journal and made a list of the "No's That Became Yes's":
1. The Morrison Industries Deal - Led to three new clients 2. Jennifer - Now officially dating 3. The Fire Station Ride-Along - Resulted in a speaking invitation at their training academy 4. The Museum After-Hours Tour - Museum director hired me as a consultant 5. The Magazine Column - Writing opportunity of a lifetime 6. The Musician's Napkin - Started daily practice, already improving 7. The Country Club (plot twist) - Rejection led to invitation from member who overheard 8. The First-Class Seat - Currently sipping champagne at 30,000 feet
What did these have in common? I wrote for the entire flight, landing on three principles:
Principle 1: Authenticity Beats Perfection Every successful "rejection" came when I was genuine about why I was asking. The polished, professional requests failed. The vulnerable, honest ones succeeded.
Principle 2: Boldness Is Magnetic People were drawn to the audacity. Even when they said no, they remembered me. Three of my yes's came from people who initially rejected me but called back later.
Principle 3: Value Goes Both Ways The successful asks inadvertently offered something valuable – entertainment, perspective, a story to tell. The magazine editor didn't just see a column; she saw content that would engage readers.
Jennifer and I discussed this phenomenon over dinner the next night. We were at a restaurant I'd never have tried to get into before – secured after the maître d' initially rejected my reservation request but called back an hour later with a cancellation.
"Maybe the universe is rewarding your courage," she suggested.
"The universe has a weird sense of humor then. I'm trying to fail."
"No," she corrected. "You're trying to not let fear of failure stop you. There's a difference. And people can sense that difference."
She was right. My energy had shifted. Where I once approached interactions with apology in my voice, I now came with curiosity. Where I once prefaced requests with "I know you'll probably say no, but...", I now led with "I have an interesting proposition."
The rejections were still coming, of course. The same week as the first-class upgrade, I accumulated some spectacular no's:
Rejection #139: Asked to speak at Harvard Business School. Response: "Perhaps start with a local community college."
Rejection #146: Requested to be a guest on major podcast. Host personally emailed to say it was the most presumptuous request he'd ever received.
Rejection #151: Asked bank for a business loan with no business plan. Loan officer kept my application as an example of what not to do.
But even the rejections were different now. They came with feedback, with humor, with connection. The Harvard rejection led to an introduction to a professor studying risk-taking behavior. The podcast host followed me on social media to watch my journey. The loan officer became a lunch buddy who taught me about business financing.
By Day 90, I'd crossed 200 rejections, but my success rate was climbing too. The spreadsheet showed a fascinating evolution:
- Days 1-30: 8% success rate - Days 31-60: 17% success rate - Days 61-90: 31% success rate
Mike called it the "Rejection Paradox" – the better you get at being rejected, the less rejected you get.
"You need to recalibrate," he advised during our Week 13 check-in. "If almost a third of your asks are succeeding, you're not aiming high enough."
He was right. I'd gotten comfortable with certain levels of rejection. Time to get uncomfortable again.
I made a new list, titled "Impossibly Bold Asks":
- Shadow a Fortune 500 CEO for a week - Get a celebrity to mentor me - Speak at an international conference with no qualifications - Get a book deal with no manuscript - Have dinner with my business hero - Get national media coverage for the rejection project - Convince a company to sponsor my experiment - Get a famous artist to collaborate on something
These felt properly impossible. These felt like guaranteed no's.
I started with the Fortune 500 CEO, sending personalized emails to ten executives I admired. Nine didn't respond. One did:
David, your request to shadow me is impractical and impossible given security protocols and scheduling. However, your project intrigues me. I'm hosting a leadership breakfast next month. Would you like to attend and share your rejection experiment with the group? - Richard
Rejection #201. But also, an invitation to speak to 50 top executives.
The pattern held even at higher levels. The more impossible the ask, the more interesting the alternative offers. It was as if the universe was playing a game: "You can't have exactly what you asked for, but here's something else interesting."
My journal entry from Day 95 captured the feeling:
I'm starting to understand something profound. The point isn't the yes or the no. The point is the ask. Each request, regardless of outcome, is expanding my world. I'm having conversations with people I never would have approached. I'm being invited into rooms I didn't know existed. I'm discovering that the space between yes and no is vast and full of possibility.
Tomorrow marks 100 days of rejections. Patricia wants the article about what I've learned. How do I explain that the biggest lesson is that I've been asking the wrong question my whole life? Instead of "What if they say no?" I should have been asking "What if they say something else entirely?"
As I drafted the magazine article that night, I realized my experiment had already succeeded in ways I hadn't anticipated. I was still collecting no's – 211 and counting – but each rejection was teaching me that the binary world of yes and no I'd lived in was an illusion.
Real life happened in the space between, in the creative negotiations, in the unexpected pivots, in the relationships formed through bold asks.
I was getting rejected more than ever before. I was also living more than ever before.
The two, it turned out, went hand in hand.